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使用Selectfluor进行氧化氟化反应:一种制备高价碘(V)氟化物的简便方法。

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides.

作者信息

Dearman Samuel M G, Li Xiang, Li Yang, Singh Kuldip, Stuart Alison M

机构信息

School of Chemistry, University of Leicester, Leicester, LE1 7RH, UK.

School of Chemical Engineering, Dalian University of Technology, No. 2 Linggong Road, Dalian, 116024, P. R. China.

出版信息

Beilstein J Org Chem. 2024 Jul 29;20:1785-1793. doi: 10.3762/bjoc.20.157. eCollection 2024.

DOI:10.3762/bjoc.20.157
PMID:39109295
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11301045/
Abstract

The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild and efficient route using Selectfluor to deliver hypervalent iodine(V) fluorides in good isolated yields (72-90%). Stability studies revealed that bicyclic difluoro(aryl)-λ-iodane was much more stable in acetonitrile- than in chloroform- , presumably due to acetonitrile coordinating to the iodine(V) centre and stabilising it via halogen bonding.

摘要

对高价碘(V)氟化物进行研究的能力主要受到传统上使用如三氟甲基次氟酸盐和三氟化溴等苛刻氟化试剂来制备它们的困难所限制。在此,我们报道了一条温和且高效的路线,使用Selectfluor以良好的分离产率(72 - 90%)得到高价碘(V)氟化物。稳定性研究表明,双环二氟(芳基)-λ-碘烷在乙腈中比在氯仿中更稳定,这可能是由于乙腈与碘(V)中心配位并通过卤键使其稳定。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/05f84ae6053a/Beilstein_J_Org_Chem-20-1785-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/c37b81b72b31/Beilstein_J_Org_Chem-20-1785-g006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/7d61f7a08033/Beilstein_J_Org_Chem-20-1785-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/d394c8657777/Beilstein_J_Org_Chem-20-1785-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/59d6fb143373/Beilstein_J_Org_Chem-20-1785-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/0bd427c6cea7/Beilstein_J_Org_Chem-20-1785-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/fd3837ce8b49/Beilstein_J_Org_Chem-20-1785-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/747bcef5a449/Beilstein_J_Org_Chem-20-1785-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/7e05a046cefc/Beilstein_J_Org_Chem-20-1785-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/05f84ae6053a/Beilstein_J_Org_Chem-20-1785-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/c37b81b72b31/Beilstein_J_Org_Chem-20-1785-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/c3c011aed501/Beilstein_J_Org_Chem-20-1785-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/7d61f7a08033/Beilstein_J_Org_Chem-20-1785-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/d394c8657777/Beilstein_J_Org_Chem-20-1785-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/59d6fb143373/Beilstein_J_Org_Chem-20-1785-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/0bd427c6cea7/Beilstein_J_Org_Chem-20-1785-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/fd3837ce8b49/Beilstein_J_Org_Chem-20-1785-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/747bcef5a449/Beilstein_J_Org_Chem-20-1785-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/7e05a046cefc/Beilstein_J_Org_Chem-20-1785-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6503/11301045/05f84ae6053a/Beilstein_J_Org_Chem-20-1785-g005.jpg

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